campbell



Feb. 27, 1940.

D. J. CAMPBELL MOLDING MACHINE Filed'May 2, 1938 9 Sheets-Sheet 1 IN VE N TOR .Da/v/uz J JAMPaA'LL A TTOR/VEKS F i D. J. CAMPBELL MOLDING MACHINE 'Filed May 2, 1938.

9 sheets-shed 2 lvwo/wto o flan/ALB J CAMPBELL D. J. CAMPBELL MOLDING momma Filed May 2, 1938 9 She ets-Sheet s {A} VEN TOR flo/v/u 12 J CAM/ 551. 1.

2; MM W A TTORNEY' Feb. 27, 1940.

1940- D. J. CAMPBELL MOLDING MACHINE 9 Sheets-Sheet 4 Filed May 2, 1938 R Y mu M NE R 55 0 V P T W H r w A 1940- I D. J. CAMPBELL MOLDING MACHINE Filed May 2, 1958' 9 Sheets-Sheet 5 INVENTOR BY I Feb. 27, 1940.

D. J. CAMPBELL MOLDING MACHINE Filed May 2, 1958 9 Sheets-Sheet 6 6 R Y mam w R M m J/ 9% A Feb. 27, 1940.

D. J. CAMPBELL 2,191,451

MOLDING MACHINE v Filed-May 2, 1958 9 SheetsSheet 8 //v VEN 70 A TTORNEV Feb. 27, 1940. D. J. CAMPBELL MOLDING MACHINE Filed May 2, 1938 9 Sheets-Sheet 9 v IN VENTOR fia/vnm 1 (hMPBELL 1, ML. W A TTORNE YS.

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and against-which a =sliding sshoe 1 9 I-1A rock shaft "80 passes throughfithe opening "l8 and 1 is mounted in bearings in -the walls'ofj thenir chamber housing-50. hn eccentri'c ill is provided on the shaft 89 fitting =-aeonoaved recess shaped therefor at the underside of the slide'blo'ckv 1-9. By rocking theshafti gil -the closure valve' block 16 maybe raised or loweredpermittin'g escape of air from the air chamber ah-82 lthrough the pa'ssages 53 when "raised, and closing against such escapeof air when lowereidpasin my previously' filed application, Serial NOS-7555688, above noted. 7 The housing Zatits' upper side ha's an opening which. is closed by a heavy cap 8-3,'-'iritegral with and upwardly extendinglfrom which is a'wall ti having sand escapeopenings 85 in its sides. -At

' the upper "end of the wall '-a heavy frame B6 is bolted securely inLpla-oe. withinithe' frame lifi a guide sleeve or frame 81 is secured-having "outwardly extending upper flanges against which the flask 88 Which'is to c'ontainl the :mold -i-s"-positioned 4 after having been turned-over or inverted, as shown in Fig. 10. Ascreen and pa'ttermcarrying frame including an outer frame iifislidable within the sleeVe R'I, and pattern-carrying bars 90 above which the patterns "91 "arelo'cated (as shown, for cam 's'haits),*and with -an air vent screen structure 92 between lthe bars 56, is connected by dependingaend pieces 93 with-ahead M v secured at the upper ends of vertical rods or posts "'95 which are slidable thrcugh sleeves positioned verticallyin the cap member-83. Such air 7 vent screen and framestructure forrns the sub ject matter of a contemporaneousapplication' filed May 2, 1933 land-bearing Serial No. 205573 and need not :be described in detail. 'Ihe'r'odser posts 95 at their lower-ends ar permanentlysecured to a vertically movable-slide block -96 which. is vpositioned within and guided in its -vertical movements by a surrounding guide frame 9! his posed within the housing 2, assh'own in Figs. 7

and 10. r

The block 96 and connectedparts is're'ciprocated through the straightening out or breaking of toggle links connected at one 'endthereto and at their opposite ends'to the bottom of the housing 1 member .2. Links 98 at :their "lower ends are secured to rock shafts 99 mounted for rocking movement in suitable bearings on'theba'se of said housing 2. Other links H!!! areeonnectedto'rock shafts :l M *mounted for rocking movement on "and a through the'blocksSB and having eccentricbear ing bushings for adjustment purposes. The links.

.98 andllllfl extend towardeachiotherandat their adjacent ends connect withiorward and rear knee or knuckle pivot rods Hi2 :and M3. The

,rods m2 and ill-3 are connected by a link M which is bowed upward' As shown in li'ig. 7;,

one of the upper shafts till I or both of'themi'f desired) carries a ratchet liflfi with which a dog 1% mounted on the 'block $18 is :adapted to 'de- .tachably engage, and thus i ho'l'd the parts in any upper position to which moved.

A piston rod Jill! is connected at "one end with the rod or shaft Hi3. Be-tween its ends it is pro vided with a piston Hi8 which is located within a cylinder Hi9, mounted on trunnions for rocking movement about a' horizontal axis, said cylinder being partly within both of the base housings I and 2. The piston rod extends through the cylinder and to the rear thereof, at its free end is threaded, and has stop nuts l H) adjustable there on. The piston rod extension passes through a lever Ill pivotally mounted at H2 near its lower end upon an arm projecting from the cylinder 1 H09. A tension :spring ll I 3 acts itoturn Y lever l M :a clockwise iiirection. said layer ill :at :its 'upperifront side is formed with a shallow concave recess [M 111 which a roller '1 t5", mounted on a lover 1 t6 which in turn is pivotally mounted on the cylinder lilfl sea'ts. The upper :end of the -lever I I5 is provided with-a horizontally extending operating-rod l lil l The spring 113 normally holds the lever l l'l in the position shown in Fig.

I 'withroller l-l i'efseated in recess H4. The rod H, however, may be moved lengthwiseiin a forward direction to thus move the lever l li to the position shown .in' Fig lOQwhertaupon the roller will move upwardly out of the :recess i M andenroller. This permits aiarther movement forwardicr to the'rightyof piston Hi8 and piston rod 10! than is permitted when the parts :areiin the position shown inwfiig. 51, .as the stop" nuts I it will come against the lever iii and stop such movement before it reaches the position shown inlFig. 10, :A stop block 118 isconnected or integral with-the 'bottomuiof the housing 2 and interpic'ses in "the path of a stop projection H9 [carried on the rod I113, limiting the movement of the piston and piston rod, and the consequent straightening-out of the toggle levers,- as shown in I0. I v V iInEth'e operationof the machineya'ssumir g the housing Bilit'o be;inlthe position shown in Fig-3, a hopper I72 filled with loose :sancl may be swung underneath the lower :end oi said housing 53 and with the lower side of the hopper over an inverted .Lfia'sk i818 placed upon the support there- :for below. ISpring this designed to hold the hopper with :its bottom slightly above the flask =38 and stops it {and ill maintain its upper end he lowzthellc'wer closingplate :50 of the aair chamber 82. xThelatch t8 'inrsuch case will ;be in latching position as in Fig. l8.- 1

, fBy energizin-g the solenoid H "the latch '68 is released -and, thereafter, by introducing compressed air above the piston Eda-the toggle links 56 andi58 will bestra'i'ghtened, :as :inFig. 3,, bringring the closure plate 52 against and in closing position above the hopper 42,, forcing the hopper downwardly so as to bring its lowerside snugly against :the'upper side' of the inverted flask 88. It

lis' to'ibe understood that when this occurs the patterns and the screen iframe carrying the same are in the position shown in Fig. 9, that is, with the upper edges of the frame '89 a short distance block T6 in a lowercposition. It ispartia-Hy halanced byan upward pressure "against the total area "of all of the pistons 14. When the valve block is raised, the compressed air passes through theQ openin'gs -at 53 and forces sand out of the shopper 12 :into the .fiask,bfilling the :same completely and covering the patterns at all vparts exposed and coming against the patterns and the air'vent screen bars 92, the sand extending within the guide frame 81 a short distance so as to not only fill the flask, but overfill it at its inverted 1 open side.

It is to be understood that while this projection gagetagai-nst the lever ith'ereabcve, as shown in l Eig. 10, 'spring l 13 rcausing thelever to t-followthe stop nuts ill] come against the lever I ll which is held latched in the position shown in Fig. 3 by the lever Ill coming against the roller H5, the axis of which is in substantially horizontal alinement with the axis of the pivot of said lever H6.

After the flask has thus been more than filled with sand the next operation is the squeezing operation. Rod H1 is moved longitudinally forward or to the right, thereby releasing the roller H5 from the recess H4, unlatching the lever Hl,-which is permitted to swing from the position in Fig, 9 to that in Fig. 10, whereupon the piston I08 moves from the position in Fig. 9 to that in Fig. 10, straightening out the toggle links 98 and 91, and moving the patterns and the associated pattern carrying and. screen frame upwardly, compressing and squeezing the sand which has previously more than filled the flask into the compass of the flask.

Following the squeezing operation it is then necessary to withdraw the patterns downwardly with a reversal of the movement of the piston I03. Reversal of movement is accomplished by entering the compressed air or other motive fluid to the right hand side of the piston, moving it back to the other end of the cylinder or from the position shown in Fig. 10 to that in Fig. 7.

This drops the pattern and the parts which carry it down to the lowest position thereof within the guide frame 8'1, shown in Fig. 7, completely clear ing the mold within the flask of the pattern. The rod 5 ll is moved longitudinally to the left, again latching the lever ill in the position shown in Figs. 3 and '7. Of course the rock shaft 85 is rocked in the opposite direction to close olf the flow of compressed air into the hopper l2 and after the pattern has been withdrawn, air is directed into the cylinder underneath the piston 66a, lifting the compressed air chamber housing 50, whereupon the hopper is elevated slightly above the flask by spring 15 ready to be swung away from between the flask and the air chamber housing 50. This swing of the flask will follow on the next intermittent rotative movement of the ring 6.

It is to be understoood that with three flasks, and with one of them" at the operative position for having sand therein forced into a flask to produce a mold, the flasks at the other positions when stopped, one of them will be at a'sand fllling'station where it is "filled with loose sand, and the other at a cleaning station wherein any excess sand left in. the hopper after a flask has been filled is removed, and the hopper otherwise cleaned before passing to the sand filling station. Thus, the process is substantially continuous, the stopping of the sand hoppers at the three consecutive stations, one for cleaning the hopper, one for filling it with loose sand, and the third for the forcing of the sand out into a flask to provide a mold, being onlyfor thetime which is consumed in these operations, all three with respect to different flasks taking place at the same time. After a hopper has had its sand discharged therefrom into a flask and has been moved away, or immediately after it has been released from the flask by the upward movement of the air chamber housing 50, the flask with the mold therein is removed and an empty inverted flask put in its place.

With the machine as described, a very practical, efficient and easily operated molding machine is produced. All of the operations may be quickly performed. The rotation of the ring 6 which carriesall of the sand hoppers may be timed so as to get the greatest quantity production of molds. This molding machine, while similar in many respects to the disclosure of the machine in my prior filed application to which reference has been made, has many marked and valuable improvements which are defined in the appended claims; and the invention is to be considered comprehensive of all forms of structure coming within the scope of such claims,

I claim:

1. In molding apparatus, a flask support adapt- -ed to have a succession of inverted flasks carried by said support, a vertical supporting post to one side of the flask support, a ring mounted for rotation around said post, a plurality of brackets projecting laterally from the ring at substantially sides are a short distance above their respective flasks when moved thereover, and means to limit the extent of lifting said hoppers.

2. A molding apparatus comprising, a support adapted to have a succession of inverted flasks carried thereby, a vertical post adjacent said support, a plurality of spaced apart sand hoppers around said post and revolubly mounted thereon, driving means for intermittently bringing said sand hoppers over a flask on said support, means to normally elevate the hoppers whereby their lower sides are a short distance above their respective flasks when moved thereover, and means to limit the extent of lifting said hoppers.

3. A molding apparatus comprising, a support adapted to have a succession of inverted flasks carried thereby, a vertical post adjacent said support, a ring mountedfor rotation around said post, a plurality of spaced apart sand hoppers mounted on said ring, means for intermittently driving the ring whereby said sand hoppers are successively brought to and over a flask on said supportpspring means to normally elevate the hoppers whereby their lower sides are a short distance above their respective flasks when moved thereover, and means to limit the extent of lifting said hoppers.

DONALD J. CAMPBELL.

' of compounds based upon and including thiazane taining Patented Feb. 27', 1940 UNI ED .srArEs OF CE f THI AZ A NE DERIVATIVES Robert De Wolf Coghill, Hamden, Conn., assignor .to Sharp &'Dohme, Incorporated, Philadelphia, Pa, a corporation of Maryland No Drawing. Applica tionjA pril 3,5193% I Serial No. 134,844

in Claims. (01. 250424331; I

This invention relates to new organicchemical compounds, and more particularly to new series 3,5-dicarboxylic acid, which may be graphically represented as follows;

' /.0H5-0H000H cal-o 00011 The new compounds included .withinathe invention are compounds based upon the thiazane 3,5-dicarboxylic'acid and include acid derivatives of this compound, such as the mono; and diesters, the mono-. and diacid amides. and halides, the nitriles, the 'nitriloamides, thesalts with bases, in which'one or -both of the carboxylic hydrogens are replaced by"metals "or nitrogen bases, salts of the esters, etc., with acids (the carboxylic acids do not form crystallizable salts with acids, because of the influence of the carboxyl groups), closely related oxidized derivatives in which the sulfur atom is'oxidized to form the corresponding sulfoxides or suliones or sulfonium salts, and corresponding series of compounds in which the nitrogen-linked hydro gen is replaced by an alkyl, aralkyl, aryl, or other cyclohydrocarbon radical, which may. be substituted or unsubstituted. Essentially, all of these new compounds are based upon the thiazane 3,5-dicarboxylic acid; and it will be at once apparent to those skilled in the art that a great number of compoundsgof the type indicated may be readily produced fromthis acid or its congeners orhomologues, particularly its acyl derivatives, such as the acid chlorides or amides, the production of whichmayor may not involve the intermediate production of the dicarboxylic acid.

The invention includes not only these new compounds but also a new process by which the compounds may be produced. Briefly, the process consists in-the treatment of an aqueous solution of 3,5-dihydroxythioxane, produced as de scribed in my companion application, Serial No. 134,843, filed April 3, 1937, and which is probably more properly described as a solution conin equilibrium 3,5-dihydroxythioxane and thiodiacetaldehyde, with ammonium cyanide, or ammonia or its congeners, such-as pri mary amines, including primary alkyl, aralkyl', aryl, or alicyclic amines, and hydrogen cyanide.

If ammonium cyanide, or hydrogen cyanide and ammonia be ,used, a nitriloamide having the probable structural formula: v

v oar-ouch:

s NH cm-onoonrn l is produced. Both the'nitrile group, and acid amide group of. this compound are cartermediates *a dY i boxylicv acid derived groups, even though the free 'a'cid jhas not been usedas anintermediate' init rdu t a v i This compound, which is valuablev as the start: ingpoint for the production of other substituted thiazane derivatives is readily hydrolyzed by con.-

centrated acid to thiazane 3,5-dicarboixylic' acid, I

having the formula: 1 I

These two compounds are both valuable as in one or both of the carboxylic acid groups either for the production of various. thiazane derivatives," including monoancli. di 1,.3 estersysuch 'as may be:produced by esterifying with simple alcohols; such as ethanol," propanol,

benzyl alcohol, or pheno1s,.'s'uch' as "phenol, cresol,

xylenol orjothermono-Ior polyhydri'cphenol, or amino alcohols, such, as dipropylaminoethanol,

cnkonoo ocom i s. i -/NH U V CHi-CHCOOCtHB l Such esters may be readily produced fromthe corresponding acid chlorides and the alcohols or phenolaor'from the dicarboxylic acid and the '"alcoholsin the presence of a suitable esterifying agent, such as hydrogen chloride. The esters of thejamino alcohols are indicatedto have local anaesthetic properties.

".Ii insteadv of ammonia in the io nnation of 'these' derivativesjprim'aryaminesbe used, corresponding N-substituted, thiazane 3,5-dicarboixylic acids are produced. Among the amines which may be used instead of ammonia, with the production of corresponding N-substituted' compounds, are. 'm'onomethylamine, monoethylamine, monopropylamine, amylamine, and" other primary alkyl amines, aniline, the toluidlnes,.the xylidenes, mes'idine, 'benzylamine, cyclohexylamine, cyclopentylamine,

monobutylamine, I mono,-

etc. The reaction of one of these primary amines and hydrogen cyanide withthiodiacetal-v dehyde and 3,5 dihydrozrythioxane results in the production of the N-substituted nitriloamides, which may be hydrolyzed to the corresponding N-substituted thiazane 3,5-dicarboxylic acids, represented by the structural formula:

CHE-0300011 s \N-R onrofiooon in which R may be an alkyl, aryl, aralkyl or other cyclohydrocarbon radical These N-substituted derivatives may also be used as inter mediates for the production of esters, such as the amino alcohol or substituted amino alcohol esters, etc.

It will be noted that the sulfur atomin these compounds has-a valence of but 2,'so that it may readily be oxidized by suitable agents such as the halogens, nitric, acid, potassium permanganate, etc., with the production of .the corresponding sulfoxides and sulfones,

The sulfoxide derivatives. are. obtained when the oxidation is carried outwith relatively mild oxidizing agents, such as dilute nitric acid, the sulfur being oxidized to a valence of 4. The sulfoxide of thiazane 3,5 dicarboxylic acid may be represented by the formula:

onrono OOH 0s carom: OOH

When more vigorous oxidizing agents, such as Thesesulfoxides and sulfonesiorm series: of

compounds related to those described above, but 1 having the suifoxide or sulfone structure; rather than the simple thiazane structure.

The sulfoxide and sulfone derivatives may also be prepared by oxidizing the acetalyl sulfide prior to the ring closure, so that the new sulfone or sulfoxide derivatives are produced directly when the ring closure is effected, rather than by the, oxidation of the corresponding 'thiazane derivatives.

The invention will be further illustrated by the following specific description of the production of the amide of3-nitrilothiazane-5-carboxylic acid and thiazane-3,5-dicarboxylic acid, although it is in no way limited thereto, as it will be immediately apparent to those skilled in the art that these products may be readily convertedjinto a great number of derivatives including derivatives such as esters, amino esters, acyl derivatives, such as the acyl chlorides and amides, salts, phenolic derivatives, sulfones, sulfozn'des, etc., by methods well known to chemists.

Emampla-Acetalylsulfide is hydrolyzed with dilute hydrochloric acid as described in my companion application Serial No. 134,843, filed April 3, 1937,with the production of an aqueous solution containing.thiodiacetaldehyde and 3,5-dihydroxythioxane in equilibrium.v Specifically, 53 parts of acetalyl sulfide are hydrolyzed with 300 parts of 6.5% hydrochloric acid by vigorously shaking at about 40 to 50 C. until solution is practically complete. The solution is filtered and concentrated under vacuumat room temperature to about the original volume, and to the Cooled concentrate are added 11.2 parts of liquid hydrogen cyanide. The mixtureis allowed to stand for a few minutes after which an aqueous solution containing 7 parts of ammonia is added slowly with stirring. The resulting solution is placed in an ice-box overnight, after which the reaction product is filtered off and recrystallized from alcohol, in which it is sparingly soluble. A crystalline solid, in the vform of yellow needles, melting with decomposition at 192 C. is obtained in good yields. This crystalline material isinsoluble in cold water and nearly all common organic solvents except boiling alcohol, but is soluble in concentrated mineral acid. When boiled with concentrated caustic soda it gives off of its nitrogen as ammonia. When boiled 'with 0.05

normal caustic soda, of the nitrogen is given off as ammonia in about 20 minutes, the second third of the nitrogen being given ofi much more slowly, only about /2 of the'second third appearing as ammonia in two hours. This crystalline solid is the-amide of 3-nitrilothiazane-5-carboxylic acid, having the structural formula:

on onon om-onoonm When this nitriloamide is heatedwith concentrated mineral acid, it'is hydrolyzed to thiazane- 3,5-dicarboxylic acid. 10 parts of the nitriloamide obtained as above are refluxed for three hours with concentrated hydrochloric acid, after which the solution is evaporated to dryness on a water bath, dissolved in water and-the solution adjusted in pH by the addition of ammonia until it is barely alkaline to Congo red. The thiazanee 3,5-dicarboxylic acid crystallizes out in white needles which are recrystallized from wateryand which contain 1 mol of water of crystallization.

The productis obtained in good yields. When heated, the crystals first decrepitate or crackle and then melt with decomposition at 253-254" C. The product has the structural formula:

orn' onooon I CHz-QHOOOH This di carboxylic acid,.as well, as the corresponding N -alkyl, N-aralkyl, N-aryl and N-alicylic acids, may be produced in stereoisomeric. forms,

that described above apparently beingthe cisor mesoform. By using somewhat higher temperatures in the production of the intermediate nitriloamide, the trans-form of theacids may be produced as mixtures of the dextroand laevoacids, which may be resolved into their constituents. These isomeric forms may be used in the same manner as the mesoform, for the production of corresponding derivatives, which in general show the usual relationship of stereoisomeric compounds. For example, if, during the treatment of the thiodiacetaldehyde and 3,5-dihydroxythioxane .With ammonia and hydrogen cyanide the temperature be permitted to rise, a nitriloamide, isomeric to that described above, but melting at 210 C. (uncon) is obtained. This, when hydrolyzed with mineral acid, yields a thiazane-3,5-dicarboxylic acid melting at 270 C. (um-on). I believe that these products are optical isomers of the products previously described, and apparently are composed of racemic mixtures of the trans-compounds. The reactions involved in the formation of the dicarboxylic acid of the 

